5-methyl-2-phenyl-4-carbaldehyde

Isoxazole-4-carbaldehyde, 6, 84 Isoxazole-4-carbaldehyde, 5-methyl-3-phenyl-oxidation, 6, 27, 53 Isoxazole-5-carbaldehyde synthesis, 6, 84 Isoxazole-3-carboxylic acid esters... 

Wittig reaction of 3-phenyl-2//-azirine-2-carbaldehyde (1) with [3-(methoxycarbonyl)prop-2-enylidene]triphenylphosphorane (2) in hot benzene yields a mixture of methyl 7-phenyl-l//-azepine-2-carboxylate (3) and the 2//-azirine4.13 Diene 4 is extremely heat sensitive and isomer-izes on standing at room temperature to the lf/-azepine 3 (see also Section 3.1.1.5.7.). 

Electrophilic substitution of the ring hydrogen atom in 1,3,4-oxadiazoles is uncommon. In contrast, several reactions of electrophiles with C-linked substituents of 1,3,4-oxadiazole have been reported. 2,5-Diaryl-l,3,4-oxadiazoles are bromi-nated and nitrated on aryl substituents. Oxidation of 2,5-ditolyl-l,3,4-oxadiazole afforded the corresponding dialdehydes or dicarboxylic acids. 2-Methyl-5-phenyl-l,3,4-oxadiazole treated with butyllithium and then with isoamyl nitrite yielded the oxime of 5-phenyl-l,3,4-oxadiazol-2-carbaldehyde. 2-Chloromethyl-5-phenyl-l,3,4-oxadiazole under the action of sulfur and methyl iodide followed by amines affords the respective thioamides. 2-Chloromethyl-5-methyl-l,3,4-oxadia-zole and triethyl phosphite gave a product, which underwent a Wittig reation with aromatic aldehydes to form alkenes. Alkyl l,3,4-oxadiazole-2-carboxylates undergo typical reactions with ammonia, amines, and hydrazines to afford amides or hydrazides. It has been shown that 5-amino-l,3,4-oxadiazole-2-carboxylic acids and their esters decarboxylate. 

The condensation of furo[3,2- ]pyrrole-type aldehydes 8g and 265-267 with hippuric acid was carried out in dry acetic anhydride catalyzed by potassium acetate as is shown in Scheme 26. The product methyl and ethyl 2-[( )-(5-oxo-2-phenyl-l,3-oxazol-5(4//)-ylidene)methyl]furo[3,2- ]pyrrol-5-carboxylates 268a-d were obtained. The course of the reaction was compared with the reaction of 5-arylated furan-2-carbaldehydes with hippuric acid. It was found that the carbonyl group attached at G-2 of the fused system 8 is less reactive than the carbonyl group in 5-arylated furan-2-carbaldehydes in this reaction <2004MOL11>. The configuration of the carbon-carbon double bond was determined using two-dimensional (2-D) NMR spectroscopic measurements and confirmed the (E) configuration of the products. 

Methyl 2-[3-(trifluoromethyl)phenyl]-4/7-furo[3,2-4]pyrrole-5-carboxylate 81a was made by thermolysis of the corresponding methyl 2-azido-3- 5-[3-(trifluoromethyl)phenyl]-2-furyl propenoate 378, which was formed by condensation of 5-[3-(trifluoromethyl)phenyl]furan-2-carbaldehyde 377 with methyl azidoacetate under sodium meth-oxide catalysis (Scheme 40) <2006KGS825>. 

In the course of the continuing study [9a,b] on the enantioselective addition of dialkylzincs to aldehydes by using chiral amino alcohols such as diphenyl(l-methyl-2-pyrrolidinyl)methanol (45) (DPMPM) [48] A. A -dibutylnorephedrine 46 (DBNE) [49], and 2-pyrrolidinyl-l-phenyl-1-propanol (47) [50] as chiral catalysts, Soai et al. reacted pyridine-3-carbaldehyde (48) with dialkylzincs using (lS,2/ )-DBNE 46, which gave the corresponding chiral pyridyl alkanols 49 with 74-86% ee (Scheme 9.24) [51]. The reaction with aldehyde 48 proceeded more rapidly (1 h) than that with benzaldehyde (16 h), which indicates that the product (zinc alkoxide of pyridyl alkanol) also catalyzes the reaction to produce itself. This observation led them to search for an asymmetric autocatalysis by using chiral pyridyl alkanol. 

Methyl-8-oxo-5-phenyl-7,8-dihydro-l,7-naphthyridine-6-carbaldehyde (4, R = CHO) also gave the acid (4, R = CO2H) (substrate, NaOH, Bu OH, H20 KMn04 in slowly 20°C, 40 min 91%).593... 

Methyl-8-oxo-5-phenyl-7,8-dihydro-1, 7-naphthyridine-6-carbaldehyde 7-Methyl-8-oxo-5-phenyl-7,8-dihydro-1, 7-naphthyridine-5-carbonitrile 7-Methyl-8-oxo-5-phenyl-7,8-dihydro-1, 7-naphthyridin-6-carboxamide 7-Methyl-8-oxo-5-phenyl-7,8-dihydro-1, 7-naphthyridin-6-carboxylic acid 5-Methyl-3-phenyl-1,7-naphthyridine... 

Acetophenone-sensitized photolysis of l-methyl-3-phenyl-2-cyclohexene-carbaldehyde oxime acetate (56) A solution of 56 (298 mg, 1.16 mmol)... 

The Pd-catalysed Miyaura-Suzuki coupling of aryltrifluoroborates with 4-tosyloxycoumarins in aqueous conditions offers an attractive route to 4-arylcoumarins <06TL1525> and 4-hydroxycoumarins have been converted into a mixture of predominantly thiopyrano[5, 4 3,4]- pyrano[5,6-c]coumarins and [6,5-c]chromones in a one-pot tandem Knoevenagel - HDA sequence with an S-prenylated 1-phenyl-lff-pyrazole-4-carbaldehyde <06TL2265>. The benzopyrano[4,3-c]benzopyranone system can be obtained from 3-aryl-4-methylcoumarins by deprotonation of the methyl function and subsequent elaboration <06TL5909>. 

Chroman, 4-( p-hydroxyphenyl)-2,2,4-trimethyl-X-ray studies, 3, 622 Chroman, 2-methoxy-synthesis, 3, 806 Chroman, 5-methoxy-synthesis, 3, 778 Chroman, 7-methoxy-synthesis, 3, 778 Chroman, 8-methoxy-acylation, 3, 732 Chroman, 2-methoxy-2-methyl-synthesis, 3, 780 Chroman, 2-methyl-synthesis, 3, 785 Chroman, 5-methyl-reactivity, 3, 732 Chroman, 6-nitro-synthesis, 3, 784 Chroman, 4-phenyl-synthesis, 3, 783 Chroman, thio-metabolism, 1, 241 Chroman, 5,6-thio-2-substituted metabolism, 1, 241 Chromanamines H NMR, 3, 580 Chroman-3-amines conformation, 3, 630 (S) -Chroman-2-carbaldehyde synthesis, 3, 779 Chromancarbaldehydes synthesis, 3, 782 Chroman-4-carbamic add synthesis, 3, 782 (R)-Chroman-2-carboxylic add methyl ester... 

The preparation and reactions of the azine, phenylhydrazone, and phenyl-semicarbazone of 4-amino-5-formyl-2-methyltriazole proceeded normally. One acetal has been prepared as follows. 4-Amino-3-benzyl-5-formyltriazole and boron trifluoride (as diethyl ether complex), stirred in methanol, gave 4-amino-3-benzyl-5-dimethoxymethyltriazole (20°C, 6 hr, 53%) and a dimeric by-product, 4-amino-3-benzyl-5-(3-benzyl-5-dimethoxytriazol-4-ylimino-methyl)triazole [73JCS(P1)2037]. The amino group in 4-aminotriazole-5-carbaldehydes lends itself readily to the formation of amidines and imidates (Section III,B,1), but it resists acylation. 

The reaction of 4-methyl-2-phenylpyrimidine-5-carboxylic acid with the reagent prepared from diethylformamide and phosphoryl chloride yields 6-ethyl-2-phenyl-5-oxo-5,6-dihydropyri-do[4,3-c/]pyrimidine-8-carbaldehyde (8), the aldehyde function in the 8-position resulting from a Vilsmeier formylation.520... 

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